The Obstacle is the Way: The Ancient Art of Turning Adversity to Advantage
Author: Holiday, Ryan
Notes by: Jacopo Perfetti.
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In the year 170,
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Marcus Aurelius, the emperor of the Roman Empire, sat down to write.
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A formula for thriving not just in spite of whatever happens but because of it.
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Our actions may be impeded … but there can be no impeding our intentions or dispositions. Because we can accommodate and adapt. The mind adapts and converts to its own purposes the obstacle to our acting.
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And then he concluded
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The impediment to action advances action. What stands in the way becomes the way.
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the secret to an art known as turning obstacles upside down.
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confront obstacles and struggle to overcome them — learning to turn those obstacles upside down.
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Whatever we face, we have a choice: Will we be blocked by obstacles, or will we advance through and over them ?

 
INTRODUCTION
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Every obstacle is unique to each of us. But the responses they elicit are the same: Fear. Frustration. Confusion. Helplessness. Depression. Anger.
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we do nothing.
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When really only one thing is at fault: our attitude and approach.
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What are we missing ? It’s simple: a method and a framework for understanding, appreciating, and acting upon the obstacles life throws at us.
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Andy Grove, former CEO of Intel,
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“Bad companies are destroyed by crisis. Good companies survive them. Great companies are improved by them.”
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The Obstacles That Lie Before Us
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“The Things which hurt,” Benjamin Franklin wrote, “instruct.”
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Today, most of our obstacles are internal, not external.
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Instead of opposing enemies, we have internal tension. We have professional frustration. We have unmet expectations. We have learned helplessness. And we still have the same overwhelming emotions humans have always had: grief, pain, loss.
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Many of our problems come from having too much: rapid technological disruption, junk food, traditions that tell us the way we’re supposed to live our lives. We’re soft, entitled, and scared of conflict. Great times are great softeners. Abundance can be its own obstacle, as many people can attest.
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Overcoming obstacles is a discipline of three critical steps. It begins with how we look at our specific problems, our attitude or approach ; then the energy and creativity with which we actively break them down and turn them into opportunities ; finally, the cultivation and maintenance of an inner will that allows us to handle defeat and difficulty.
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Perception, Action, and the Will.

 
PART I Perception
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PERCEPTION ? It’s how we see and understand what occurs around us — and what we decide those events will mean.
THE DISCIPLINE OF PERCEPTION
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Desperation, despair, fear, powerlessness — these reactions are functions of our perceptions. You must realize: Nothing makes us feel this way ; we choose to give in to such feelings.
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Too often we react emotionally, get despondent, and lose our perspective. All that does is turn bad things into really bad things.
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Discipline in perception lets you clearly see the advantage and the proper course of action in every situation — without the pestilence of panic or fear.
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There are a few things to keep in mind when faced with a seemingly insurmountable obstacle. We must try: To be objective To control emotions and keep an even keel To choose to see the good in a situation To steady our nerves To ignore what disturbs or limits others To place things in perspective To revert to the present moment To focus on what can be controlled
RECOGNIZE YOUR POWER
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Our perceptions are the thing that we’re in complete control of.
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Which is to say, we are never completely powerless.
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“Nothing either good or bad, but thinking makes it so,” as Shakespeare put it.
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A mistake becomes training.
STEADY YOUR NERVES
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as Voltaire once explained
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“tranquil courage in the midst of tumult and serenity of soul in danger, which the English call a cool head.”
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nerve is also a matter of acceptance :
CONTROL YOUR EMOTIONS
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When people panic, they make mistakes.
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Some of us almost crave sounding the alarm, because it’s easier than dealing with whatever is staring us in the face.
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So panic has to be trained out. And it does not go easily.
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Uncertainty and fear are relieved by authority. Training is authority.
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The Greeks had a word for this: apatheia. It’s the kind of calm equanimity that comes with the absence of irrational or extreme emotions. Not the loss of feeling altogether, just the loss of the harmful, unhelpful kind.
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If you need to take a moment, by all means, go ahead. Real strength lies in the control or, as Nassim Taleb put it, the domestication of one’s emotions, not in pretending they don’t exist.
PRACTICE OBJECTIVITY
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Don’t let the force of an impression when it first hit you knock you off your feet ; just say to it: Hold on a moment ; let me see who you are and what you represent. Let me put you to the test. — EPICTETUS
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Miyamoto Musashi
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In The Book of Five Rings, he notes the difference between observing and perceiving. The perceiving eye is weak, he wrote ; the observing eye is strong.
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The observing eye sees events, clear of distractions, exaggerations, and misperceptions. The perceiving eye sees “insurmountable obstacles” or “major setbacks” or even just “issues.”
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The Stoics use contempt as an agent to lay things bare and “to strip away the legend that encrusts them.”
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Epictetus told his students, when they’d quote some great thinker, to picture themselves observing the person having sex.
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Objectivity means removing “you” — the subjective part — from the equation. Just think, what happens when we give others advice ? Their problems are crystal clear to us, the solutions obvious.
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Take your situation and pretend it is not happening to you. Pretend it is not important, that it doesn’t matter.
ALTER YOUR PERSPECTIVE
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Perspective has two definitions. Context: a sense of the larger picture of the world, not just what is immediately in front of us Framing: an individual’s unique way of looking at the world, a way that interprets its events
IS IT UP TO YOU ?
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In life our first job is this, to divide and distinguish things into two categories: externals I cannot control, but the choices I make with regard to them I do control. Where will I find good and bad ? In me, in my choices. — EPICTETUS
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what if you focused on what you can change ? That’s where you can make a difference.
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what is up to us ? Our emotions Our judgments Our creativity Our attitude Our perspective Our desires Our decisions Our determination
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What is not up to us ? Well, you know, everything else.
LIVE IN THE PRESENT MOMENT
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The point is that most people start from disadvantage (often with no idea they are doing so) and do just fine. It’s not unfair, it’s universal. Those who survive it, survive because they took things day by day — that’s the real secret.
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Don’t waste time on false constructs.
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whether this is the worst time to be alive or the best,
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What matters is that right now is right now.
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You have to work at it. Catch your mind when it wanders — don’t let it get away from you.
THINK DIFFERENTLY
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what if the “other” party is wrong ? What if conventional wisdom is too conservative ?
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An entrepreneur is someone with faith in their ability to make something where there was nothing before.
FINDING THE OPPORTUNITY
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It’s our preconceptions that are the problem. They tell us that things should or need to be a certain way, so when they’re not, we naturally assume that we are at a disadvantage or that we’d be wasting our time to pursue an alternate course. When really, it’s all fair game, and every situation is an opportunity for us to act.
PREPARE TO ACT
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Once you see the world as it is, for what it is, you must act.

 
PART II ACTION
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As a discipline, it’s not any kind of action that will do, but directed action. Everything must be done in the service of the whole.
THE DISCIPLINE OF ACTION
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Some academic once asked Demosthenes what the three most important traits of speechmaking were. His reply says it all: “Action, Action, Action !”
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We forget: In life, it doesn’t matter what happens to you or where you came from. It matters what you do with what happens and what you’ve been given. And the only way you’ll do something spectacular is by using it all to your advantage.
GET MOVING
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We often assume that the world moves at our leisure. We delay when we should initiate.
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So the first step is: Take the bat off your shoulder and give it a swing. You’ve got to start, to go anywhere.
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And that’s the final part: Stay moving, always.
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So when you’re frustrated in pursuit of your own goals, don’t sit there and complain that you don’t have what you want or that this obstacle won’t budge. If you haven’t even tried yet, then of course you will still be in the exact same place. You haven’t actually pursued anything.
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all the greats you admire started by saying, Yes, let’s
PRACTICE PERSISTENCE
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In persistence, he’d not only broken through: In trying it all the wrong ways, Grant discovered a totally new way — the way that would eventually win the war.
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In 1878, Thomas Edison wasn’t the only person experimenting with incandescent lights. But he was the only man willing to test six thousand different filaments —
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he eventually found it — proving that genius often really is just persistence in disguise.
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Knowing that eventually — inevitably — one will work.
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it was the slow pressure, repeated from many different angles, the elimination of so many other more promising options, that slowly and surely churned the solution to the top of the pile.
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a phrase favored by Epictetus: “persist and resist.” Persist in your efforts. Resist giving in to distraction, discouragement, or disorder.
ITERATE
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In Silicon Valley, start - ups don’t launch with polished, finished businesses. Instead, they release their “Minimum Viable Product” (MVP) —
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As engineers now like to quip: Failure is a Feature.
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The old way of business — where companies guess what customers want from research and then produce those products in a lab, isolated and insulated from feedback — reflects a fear of failure and is deeply fragile in relation to it.
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The MVP model, on the other hand, embraces failure and feedback.
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It means iterating, failing, and improving. Our capacity to try, try, try is inextricably linked with our ability and tolerance to fail, fail, fail.
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Great entrepreneurs are: never wedded to a position
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never afraid to lose a little of their investment never bitter or embarrassed never out of the game for long
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They slip many times, but they don’t fall.
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The one way to guarantee we don’t benefit from failure — to ensure it is a bad thing — is to not learn from it. To continue to try the same thing over and over (which is the definition of insanity for a reason).
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Listen. Lessons come hard only if you’re deaf to them. Don’t be.
FOLLOW THE PROCESS
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It says: Okay, you’ve got to do something very difficult. Don’t focus on that. Instead break it down into pieces. Simply do what you need to do right now. And do it well. And then move on to the next thing. Follow the process and not the prize.
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Being trapped is just a position, not a fate.
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The process is about doing the right things, right now. Not worrying about what might happen later, or the results, or the whole picture.
DO YOUR JOB, DO IT RIGHT
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Everything is a chance to do and be your best. Only self - absorbed assholes think they are too good for whatever their current station requires.
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To whatever we face, our job is to respond with: hard work honesty helping others as best we can
WHAT’S RIGHT IS WHAT WORKS
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You’ve got your mission, whatever it is. To accomplish it,
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Sometimes that requires ignoring some outdated regulations or asking for forgiveness from management later rather than for permission (which would be denied) right now.
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Pragmatism is not so much realism as flexibility. There are a lot of ways to get from point A to point B. It doesn’t have to be a straight line. It’s just got to get you where you need to go. But so many of us spend so much time looking for the perfect solution that we pass up what’s right in front of us.
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As Deng Xiaoping once said, “I don’t care if the cat is black or white, so long as it catches mice.”
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Don’t think small, but make the distinction between the critical and the extra.
IN PRAISE OF THE FLANK ATTACK
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In only 6 of the 280 campaigns was the decisive victory a result of a direct attack on the enemy’s main army.
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From everywhere else.
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From the unexpected.
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From the untraditional.
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Remember, sometimes the longest way around is the shortest way home.
USE OBSTACLES AGAINST THEMSELVES
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Opposites work. Nonaction can be action. It uses the power of others and allows us to absorb their power as our own. Letting them — or the obstacle — do the work for us.
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So instead of fighting obstacles, find a means of making them defeat themselves.
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We get so consumed with moving forward that we forget that there are other ways to get where we are heading.
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We wrongly assume that moving forward is the only way to progress, the only way we can win. Sometimes, staying put, going sideways, or moving backward is actually the best way to eliminate what blocks or impedes your path.
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Making a negative into a positive.
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The difference is simply a shift in action and approach.
CHANNEL YOUR ENERGY
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Toussaint Louverture, the former Haitian slave turned general, so exasperated his French enemies that they once remarked: “Cet homme fait donc l’ouverture partout” (“This man makes an opening everywhere”).
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What you must do is learn how to press forward precisely when everyone around you sees disaster.
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[ A ] crisis provides the opportunity for us to do things that you could not do before.”
PREPARE FOR NONE OF IT TO WORK
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Perceptions can be managed. Actions can be directed.
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Problems, as Duke Ellington once said, are a chance for us to do our best. Just our best, that’s it. Not the impossible.

 
PART III Will
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Will is our internal power, which can never be affected by the outside world.
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If action is what we do when we still have some agency over our situation, the will is what we depend on when agency has all but disappeared.
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Abraham Lincoln battled crippling depression his entire life. Known at the time as melancholy,
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he found purpose and relief in a cause bigger than himself and his personal struggles.
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“This too shall pass” was Lincoln’s favorite saying,
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This was Lincoln: always ready with a new idea or innovative approach
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but equally prepared for the worst.
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The will is the one thing we control completely, always.
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We can think, act, and finally adjust to a world that is inherently unpredictable. The will is what prepares us for this, protects us against it, and allows us to thrive and be happy in spite of it.
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It’s what allows us to stand undisturbed while others wilt and give in to disorder.
BUILD YOUR INNER CITADEL
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By age twelve, Theodore Roosevelt had spent almost every day of his short life struggling with horrible asthma.
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look at his father and say with determination: “I’ll make my body.”
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It was the beginning of his preparation for and fulfillment of what he would call “the Strenuous Life.”
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We take weakness for granted. We assume that the way we’re born is the way we simply are, that our disadvantages are permanent. And then we atrophy from there.
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Consider the line from the Haggadah: “In every generation a person is obligated to view himself as if he were the one who went out of Egypt.”
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what the Stoics called the Inner Citadel, that fortress inside of us that no external adversity can ever break down.
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An important caveat is that we are not born with such a structure ; it must be built and actively reinforced.
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the way to strengthen an arch is to put weight on it — because it binds the stones together, and only with tension does it hold weight —
ANTICIPATION (THINKING NEGATIVELY)
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technique designed by psychologist Gary Klein known as a premortem.
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In a postmortem,
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We’re examining the project in hindsight, after it happened.
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A premortem is different. In it, we look to envision what could go wrong, what will go wrong, in advance, before we start.
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Mike Tyson, who, reflecting on the collapse of his fortune and fame, told a reporter, “If you’re not humble, life will visit humbleness upon you.”
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Stoics. They even had a better name: premeditatio malorum (premeditation of evils).
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Seneca
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“Nothing happens to the wise man against his expectation,”
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manage expectations. Because sometimes the only answer to “What if…” is, It will suck but we’ll be okay.
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The only guarantee, ever, is that things will go wrong. The only thing we can use to mitigate this is anticipation. Because the only variable we control completely is ourselves.
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We are prepared for failure and ready for success.
THE ART OF ACQUIESCENCE
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It doesn’t always feel that way but constraints in life are a good thing. Especially if we can accept them and let them direct us. They push us to places and to develop skills that we’d otherwise never have pursued.
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When the cause of our problem lies outside of us, we are better for accepting it and moving on.
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The Stoics
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call it the Art of Acquiescence.
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It takes a real man or woman to face necessity.
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Yet we squirm and complain about what was taken from us. We still can’t appreciate what we have.
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As Francis Bacon once said, nature, in order to be commanded, must be obeyed.
LOVE EVERYTHING THAT HAPPENS: AMORFATI
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A fire had broken out at Edison’s research and production campus a few miles away.
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Edison calmly but quickly made his way to the fire,
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looking for his son. “Go get your mother and all her friends,” he told his son with childlike excitement. “They’ll never see a fire like this again.” What ? ! Don’t worry, Edison calmed him. “It’s all right. We’ve just got rid of a lot of rubbish.”
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Within about three weeks, the factory was partially back up and running.
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He not only suffered a spectacular disaster, but he recovered and replied to it spectacularly.
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It is the act of turning what we must do into what we get to do.
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As the Stoics commanded themselves: Cheerfulness in all situations, especially the bad ones.
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The goal is: Not: I’m okay with this. Not: I think I feel good about this. But: I feel great about it. Because if it happened, then it was meant to happen, and I am glad that it did when it did. I am meant to make the best of it.
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We don’t get to choose what happens to us, but we can always choose how we feel about it.
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Edison
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They didn’t simply roll over and tolerate adversity. They accepted what happened to them. They liked it.
PERSEVERANCE
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Perseverance is
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about what happens not just in round one but in round two and every round after — and then the fight after that and the fight after that, until the end.
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The Germans have a word for it: Sitzfleisch. Staying power. Winning by sticking your ass to the seat and not leaving until after it’s over.
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Persistence is an action. Perseverance is a matter of will. One is energy. The other, endurance.
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And, of course, they work in conjunction with each other.
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We’re crushed when what we were “promised” is revoked — as if that’s not allowed to happen.
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Beethoven: “The barriers are not erected which can say to aspiring talents and industry, Thus far and no farther.”
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Our actions can be constrained, but our will can’t be.
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Churchill’s old acronym: KBO. Keep Buggering On.
SOMETHING BIGGER THAN YOURSELF
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when we are personally stuck with some intractable or impossible problem, one of the best ways to create opportunities or new avenues for movement is to think: If I can’t solve this for myself, how can I at least make this better for other people ?
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How can we use this situation to benefit others ?
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What doesn’t help anyone is making this all about you, all the time.
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Because now we have something to do.
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This kind of myopia is what convinces us, to our own detriment, that we’re the center of the universe. When really, there is a world beyond our own personal experience filled with people who have dealt with worse.
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You can always remember that a decade earlier, a century earlier, a millennium earlier, someone just like you stood right where you are and felt very similar things, struggling with the very same thoughts.
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Embrace this power, this sense of being part of a larger whole.
MEDITATE ON YOUR MORTALITY
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In late 1569,
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Michel de Montaigne was given up as dead after being flung from a galloping horse.
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Man nearly dies, he takes stock, and emerges from the experience a completely different, and better, person.
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Death doesn’t make life pointless, but rather purposeful.
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embracing the precariousness of our own existence can be exhilarating and empowering.
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We may not say it, but deep down we act and behave like we’re invincible.
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That stuff happens to other people, not to ME. I have plenty of time left.
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thinking about and being aware of our mortality creates real perspective and urgency. It doesn’t need to be depressing. Because it’s invigorating.
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Reminding ourselves each day that we will die helps us treat our time as a gift.
PREPARE TO START AGAIN
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The great law of nature is that it never stops. There is no end. Just when you think you’ve successfully navigated one obstacle, another emerges.
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As the Haitian proverb puts it: Behind mountains are more mountains.
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Knowing that life is a marathon and not a sprint is important. Conserve your energy.
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we get better with every attempt.

 
FINAL THOUGHTS
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This,
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is the pattern in every one of the stories in this book.
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Something stands in someone’s way. They stare it down, they aren’t intimidated. Leaning into their problem or weakness or issue, they give everything they have, mentally and physically. Even though they did not always overcome it in the way they intended or expected, each individual emerged better, stronger.
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We can see the “bad” things that happen in our lives with gratitude and not with regret because we turn them from disaster to real benefit — from defeat to victory.
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Nassim Nicholas Taleb defined a Stoic as someone who “transforms fear into prudence, pain into transformation, mistakes into initiation and desire into undertaking.”
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Vires acquirit eundo (We gather strength as we go).
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the Soviet poet,
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Joseph Brodsky
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Marcus Aurelius
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“if Meditations is antiquity, it is we who are the ruins.”